Ethylidene diacetate as bacteriostat in cosmetic and other compositions



ETHYLIDENE DIA'CETATE AS BACTERIOSTAT IN COSMETIC AND OTHER COMPOSITIONSHoward G. Zbornik, Caldwell, and Joseph J. Cahill, Jr.,

Colonia, N.J., assignors to Celanese Corporation of America, New York,N.Y., a corporation of Delaware No Drawing. Filed Dec. 4, 1961, Scr. No.156,992 21 Claims. (Cl. 167-85) This invention relates to bacteriostatcompositions. It more particularly relates to the use of ethylidenediacetate as a bacteriostat in certain applications.

These novel bacteriostat uses of ethylidene diacetate include cosmetics,toilet articles, household products, paints, coatings, paper products,foods, agricultural products, metal working fluids, plastics fibers andfabrics, and the like.

Ethylidene diacetate is an effective bacteriostat when employed fromabout 0.01% to by weight of the product in the above noted uses. Incosmetics, food, toilet articles, household products, fabrics and thelike, it is desirable to maintain the proportion of ethylidene diacetatetoward the lower end of this range with about 0.01 to 0.03 weightpercent being preferred. In various industrial uses, such as'for examplemetal working fluids, agricultural products, some paper products, somepaints, plastics and coatings, it is desirable to maintain theproportion of ethylidene diacetate at about 0.5 to 2 weight percent.Still other industrial applications of ethylidene diacetate as abacteriostat permit the use of this material in proportions up to about5 weight percent of the product. Of particular importance in thisconnection is the use of ethylidene diacetate to prevent slime formationin the paperindu's'try 'arfd in the treatment of soil to control pests,bacteria and fungus growth.

Other specific bacteriocidal uses of ethylidene diacetate includeshampoos, lotions, hair spray, deodorants, soaps,

6 detergents, shaving creams, insecticides, insect repellants,

\ a t er base aints facial and toilet tissue, sanitary napkins, cotTdnswabs, leather articles, cheese, cheese wrappings, garment bag coatings,metal cutting or grinding fluids, fiber sizing, particularly starchsizings, mouth wash, fabric conditions, algaecide and others.

Soaps which are rendered bacteriostatic by the practice of thisinvention are generally characteriied as being salts of fatty acids,particularly sodium potassium or ammonium salts, which have beencompounded with other constituents, such as perfumes for example, toproduce a marketable product. By detergents is meant anionic, cationicand nonionic detergents the formulations of which may in some instancesincludeinorgaic phospha-tes. Anionic detergents are exemplified by thecommercial heavy duty household products such as that sold under thetrademark Tide and are generally mixtures of alkyl aryl sulfonates andhigher alcohol sulfates (e.g. C-12 alcohols). Cationic detergentsgenerally find use in industrial cleaning particularly in the textileindustry and are generally quaternary ammonium salts such as cetylpyridinium chloride. Nonionic detergents are ex emplified by ethyleneoxide adducts of fatty alcohols or long chain aliphatic phenols (e.g.octadecyl phenol).

The following specificformulations serve to illustrate this inventionbut are in no way limiting thereon. All proportions are weight percentunless otherwise specified.

Cleansing cream Percent Beeswax 9 Parafiin l 0 Mineral oil 30 Cetylalcohol 1 Deltyl extra 10 3,250,681 Patented May 10, 1966 PercentEthylidene diacetate 0.5 Borax 1 Water 38 Perfume 0.5

Suntan lotion Glyceryl p-aminobenzoate 3 Propylene glycol ricinoleate l0Glycerol 10 Alcohol 65 Water l0 Ethylidene diacetate 2 Shampoo Coconutoil .14 Olive oil 3 Castor oil 3 Potassium hydroxide 4.7 Glycerol 2Ethanol -4 Sodium hexametaphosphate 1 Perfume 0.3 Ethylidene diacetate0.2 Water 67.8

Oil base paint Titanium dioxide 26 Zinc oxide 2.75 Varnish 53.26 Liquiddrier 2.49 Mineral spirits 13 Ethylidene diacetate 2.0

Water base paint Propylene glycol 5.12 Potassium tripolyphosphate 0.1725% Tamol 731 0.67 Potassium carbonate 0.34 Ethylidene diacetate 2.20Methyl cellulose (2% aqueous solution) 17.10 Titanium dioxide 38.50ASP-400 8.55 Duramite 8.55 Celite 281 4.28 Nopco NDW 0.67 Water 13.85

Mouth wash Glycerol 20 Ascorbic acid 0.10 Ethylidene diacetate 0.10Clove oil .02 Methyl salicylate .02 Ethanol 18 Water 61.76

Metal cutting fluid 18 parts by weight polyoxyethylene adduct of castoroil having a specific gravity of 0.98 to 0.985, a viscosity of 30S cs.,an hydroxyl value of to and 18 percent combined ethylene oxide;

18 parts by weight polyoxyethylene adduct of castor oil having 40%combined ethylene oxide, a viscosity of 230 cs., a specific gravity at25 C. of 1.015 to 1.017

and an hydroxyl value of 108 to 115;

5 parts by weight tertiary nonyl polysulfide;

5 parts by weight petroleum sulphonate;

54 parts by weight dipropylene glycol;

0.02 part by weight of dye;

5 parts by weight ethylidene diacetate;

0.15 part by weight masking agent; and

40 parts by Weight water.

Wulvll navy-m Two hundred milliliters of the emulsion as described abovewas mixed with one level teaspoon of degerminated corn meal and themixture allowed to stand in a dark cabinet at ambient temperatures for30 days during which time no rancidity was observed. In contrast to thisan identical metal cutting fluid, without ethylidene diacetate, whenadmixed with cornmeal as described above, showed rancidity in 12 to 24hours.

It is to be understood that the foregoing detailed description is givenmerely by way of illustration and that many variations may be madetherein without departing from the spirit of our invention.

Having described our invention what we desire to secure by LettersPatent is:

1. A water base metal working fluid containing ethylidene diacetate as abacteriostat.

2. A fluid as claimed in claim 1 wherein said ethylidene diacetateconstitutes about 0.01 to about weight percent thereof.

3. A fluid as claimed in claim 1 wherein said ethylidene diacetateconstitutes about 0.5 to about 2 weight percent thereof.

4. In the process of working metals using' a water based functionalfluid as the metal working fluid; the improvement which comprises theincorporation of ethylidene diacetate as a bacteriostatin said metalworking fluid.

5. A polyoxyethylene adduct of castor oil-dipropylene glycol metalcutting fluid containing ethylidene diacetate as a bacteriostat.

6. A cosmetic containing as a bacteriostat therein ethylidene diacetate.

7. Paint containing as a bacteriostat therein ethylidene diacetate.

8. Soap containing as a bacteriostat therein ethylidene diacetate.

9. Paper containing as a bacteriostat therein ethylidene diacetate.

10. The process of preventing slime formation in papermanufacturingequipment containing paper-making stock, which process comprisesincorporating ethylidene diacetate into said stock as a bacteriostat.

11. The process of controlling earth bacteria and fungus which comprisestreating said earth bacteria and fungus with ethylidene diacetate.

12. A fiber protected against mildew by impregnation with ethylidenediacetate.

13. A plastic having ethylidene diacetate applied thereto as abacteriostat.

14. A cleansing cream having ethylidene diacetate therein.

15. A suntan lotion having ethylidene diacetate therein.

16. A shampoo having ethylidene diacetate therein.

17. A mouth wash having ethylidene diacetate therein.

18. A water base paint having up to about 5% ethylidene diacetatetherein.

19. The process of controlling algae in running water which comprisesadding ethylidene diacetate to said water.

20. The process claimed in claim 19 wherein said water is in a swimmingpool.

21. A detergent having ethylidene diacetate admixed therewith.

References Cited by the Examiner UNITED STATES PATENTS 1,873,365 8/1932Fargher et al 106-15 2,390,408 12/1945 Young 106-15 2,390,887 12/1945Kling 106-15 2,474,412 6/1949 Berswo'rth 252-106 2,519,747 8/1950 DuBois 252-106 2,578,210 12/1951 Silva 167-85 2,617,769 11/1952 Nichols etal. 252-395 2,628,197 2/ 1953 Killingsworth 252-495 2,692,231 10/1954Stayner et a1. 210-64 2,711,397 6/1955 Owen et al. 167-87 XR 2,749,2766/ 1956 Novak et al. 167-85 2,756,647 7/1956 Thompson Q. 162-1612,767,088 10/1956 Crandall 162-161 2,840,503 6/1958 Whetstone et al.167-22 XR 2,919,200 12/1959 Dubin et al. 106-15 2,921,882 1/1960 Leedset al. 167-87 XR 2,921,885 1/1960 Bouchal 167-93 3,085,043 4/1963 Beaveret al. 167-22 3,085,928 4/1963 Hausweiler 167-22 OTHER REFERENCESNoller: Chemistry of Organic Compounds, W. B. Saunders Co.,Philadelphia, Pa. (1957), p. 164.

JULIAN S. LEVITT, Primary Examiner. FRANK CACCIAPAGLIA, JR., Examiner.VERA C. CLARKE, Assistant Examiner.

15. A SUNTAN LOTION HAVING ETHYLIDENE DIACETATE THEREIN.